Phenyl thioxochloroformate → HCID 19832738, compound

HRID 2051134Notes

Reaction equation

HRID 2051134 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][Si](C)(C)C)[CH:4]=1.C1(O[C:23](Cl)=[S:24])C=CC=CC=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]=[C:23]=[S:24])[CH:4]=1

Participants

4

Reactant 2

HCID 70498Phenyl thioxochloroformateHCID 19832731HCID 19832731, compound

Product 1

HCID 19832738HCID 19832738, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 300 ml of acetonitrile are added 45.0 g of 4,6-dimethoxy-2trimethylsilylaminopyridine and 35.0 g of phenylchlorothiocarbonate, followed by refluxing for 10 hours. The reaction solution is concentrated under reduced pressure to remove acetonitrile, and to the residue is added 300 ml of toluene. Insoluble product is filtered off, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel chromatography (eluent: ethyl acetate-hexane) to give 17.0 g of the title Compound. mp. 85°-86° C.

Workup

  1. temperatureby refluxing for 10 hours
  2. concentrationThe reaction solution is concentrated under reduced pressure
  3. customto remove acetonitrile
  4. additionto the residue is added 300 ml of toluene
  5. filtrationInsoluble product is filtered off
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-8173b047e9794031abedb10cd8f9a43c
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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